A direct annulation reaction of N‐(2‐formylaryl)indoles has been developed, which can provide a new entry to biologically and medicinally important indole‐indolone scaffolds via a silver‐catalyzed direct oxidative coupling between aldehyde C? H and sp2 C? H bonds for the first time. Remarkably, this strategy displayed excellent functional group compatibilities, thereby suggesting its wide potential for applications in developing and synthesizing new drug‐like compounds containing indole‐indolone frameworks.